US12210283B2ActiveUtilityA1

EUV photoresist with low-activation-energy ligands or high-developer-solubility ligands

68
Assignee: TAIWAN SEMICONDUCTOR MFG CO LTDPriority: Aug 28, 2019Filed: May 22, 2023Granted: Jan 28, 2025
Est. expiryAug 28, 2039(~13.1 yrs left)· nominal 20-yr term from priority
H10P 76/2041G03F 7/32G03F 7/2004G03F 7/16G03F 7/325G03F 7/70033G03F 7/004C07F 9/92C07F 9/90C07F 7/2208C07F 5/00C07F 3/00C07F 1/10G03F 7/0046G03F 7/0042G03F 7/027H01L 21/0274
68
PatentIndex Score
0
Cited by
25
References
20
Claims

Abstract

A photoresist includes a core group that contains metal, and one or more first ligands or one or more second ligands attached to the core group. The first ligands each have a following structure: The second ligands each have a following structure: {circle around (M)} represents the core group. L′ represents a chemical that includes 0-2 carbon atoms saturated by Hydrogen (H) or Fluorine (F). L represents a chemical that includes 1-6 carbon atoms saturated by H or F. L″ represents a chemical that includes 1-6 carbon atoms saturated by H. L″′ represents a chemical that includes 1-6 carbon atoms saturated by H or F. Linker represents a chemical that links L″ and L″′ together.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A photoresist, comprising:
 a metal-containing component; and 
 one or more ligands coupled to the metal-containing component; 
 wherein each ligand in a subset of the one or more ligands includes: 
 a first chemical coupled to the metal-containing component, wherein the first chemical includes carbon and hydrogen; 
 a second chemical that includes carbon, wherein the second chemical further includes hydrogen or fluorine; and 
 a linker that is linked to both the first chemical and the second chemical, wherein the linker includes:
 a first compound that contains —C(═O)SH; or 
 a second compound that contains —SO 2 OH, or —SO 2 SH. 
 
 
     
     
       2. The photoresist of  claim 1 , wherein the metal-containing component contains Caesium (Cs), Barium (Ba), Lanthanum (La), Cerium (Ce), Indium (In), Silver (Ag), or Antimony (Sb). 
     
     
       3. The photoresist of  claim 1 , wherein the photoresist is an extreme ultraviolet (EUV) lithography photoresist. 
     
     
       4. The photoresist of  claim 1 , wherein:
 the subset of the one or more ligands is a first subset of the ligands; 
 the one or more ligands further includes a second subset; 
 each ligand in the second subset of the ligands includes the first chemical and the second chemical; and 
 the first chemical and the second chemical are coupled together without the linker. 
 
     
     
       5. The photoresist of  claim 4 , wherein the metal-containing component is simultaneously attached to a first ligand from the first subset and a second ligand from the second subset. 
     
     
       6. The photoresist of  claim 5 , wherein:
 the metal-containing component includes a first metal ion and a second metal ion; 
 the first ligand is attached directly to the first metal ion; and 
 the second ligand is attached directly to the second metal ion. 
 
     
     
       7. The photoresist of  claim 4 , wherein the ligands in the first subset have one of the following chemical formulas: 
       
         
           
           
               
               
           
         
         wherein {circle around (M)} represents the metal-containing component. 
       
     
     
       8. The photoresist of  claim 4 , wherein the ligands in the second subset have one of the following chemical formulas: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein {circle around (M)} represents the metal-containing component. 
       
     
     
       9. A photoresist, comprising
 a metal-containing component; 
 one or more ligands attached to the metal-containing component; 
 wherein each ligand in a subset of the one or more ligands has one of the following chemical formulas: 
 
       
         
           
           
               
               
           
         
         wherein represents the metal-containing component; and 
         a linker that includes:
 a first compound that contains —C(═O)SH: or 
 a second compound that contains —SO 2 OH, or —SO 2 SH. 
 
       
     
     
       10. The photoresist of  claim 9 , wherein: the metal-containing component contains Caesium (Cs), Barium (Ba), Lanthanum (La), Cerium (Ce), Indium (In), Tin (Sn), Silver (Ag), or Antimony (Sb). 
     
     
       11. The photoresist of  claim 9 , wherein:
 the metal-containing component contains a plurality of metal ions; 
 the one or more ligands belong to a first subset of ligands that are attached to a first one of the metal ions; 
 the photoresist further includes a second subset of ligands that are attached to a second one of the metal ions; and 
 the second subset of ligands each have one of the following chemical formulas: 
 
       
         
           
           
               
               
           
         
       
     
     
       12. The photoresist of  claim 9 , wherein the photoresist is an extreme ultraviolet (EUV) lithography photoresist. 
     
     
       13. A method, comprising:
 forming a photoresist material over a substrate, wherein the photoresist material contains a metal-containing component and one or more ligands coupled to the metal-containing component; and 
 performing an extreme ultraviolet (EUV) lithography process using the photoresist material; 
 wherein each ligand in a subset of the one or more ligands includes: 
 a first chemical coupled to the metal-containing component, wherein the first chemical includes carbon and hydrogen; 
 a second chemical that includes carbon, wherein the second chemical further includes hydrogen or fluorine; and 
 a linker that is linked to both the first chemical and the second chemical, wherein the linker includes:
 a first compound that contains —C(═O)SH; or 
 a second compound that contains —SO 2 OH, or —SO 2 SH. 
 
 
     
     
       14. The method of  claim 13 , wherein the metal-containing component contains Caesium (Cs), Barium (Ba), Lanthanum (La), Cerium (Ce), Indium (In), Silver (Ag), or Antimony (Sb). 
     
     
       15. The method of  claim 13 , wherein:
 the subset of the one or more ligands is a first subset of the ligands; 
 the one or more ligands further includes a second subset; 
 each ligand in the second subset of the ligands includes the first chemical and the second chemical; and 
 the first chemical and the second chemical are coupled together without the linker. 
 
     
     
       16. The method of  claim 15 , wherein:
 the metal-containing component is simultaneously attached to a first ligand from the first subset and a second ligand from the second subset; 
 the metal-containing component includes a first metal ion and a second metal ion; 
 the first ligand is attached directly to the first metal ion; and 
 the second ligand is attached directly to the second metal ion. 
 
     
     
       17. The method of  claim 15 , wherein the ligands in the first subset have one of the following chemical formulas: 
       
         
           
           
               
               
           
         
         wherein {circle around (M)} represents the metal-containing component. 
       
     
     
       18. The method of  claim 15 , wherein the ligands in the second subset have one of the following chemical formulas: 
       
         
           
           
               
               
           
         
         wherein {circle around (M)} represents the metal-containing component. 
       
     
     
       19. The method of  claim 13 , wherein the EUV process includes an exposure process, and wherein the one or more ligands are cleaved from the metal-containing component after the exposure process. 
     
     
       20. The method of  claim 13 , further comprising cleaving the one or more ligands from the metal-containing component at least in part via a heat treatment process.

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